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Search results; Over 1,000 homes in Chicago

Flat in Chicago
Charming studio steps from WrigleyField
Studio, 1 bed, 1 private bathroom
17–22 Aug
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4.52 out of 5 average rating, 54 reviews
Superhost
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 118 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
27 Dec – 1 Jan
4.95 out of 5 average rating, 127 reviews
Guest favourite
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
30 Aug – 4 Sept
4.88 out of 5 average rating, 8 reviews
Superhost
Flat in Chicago
The Velvet Manor | Luxe 3BR • Jacuzzi • Garage
3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
New place to stay
Top guest favourite
Flat in Berwyn
Cozy, Sunny, and Clean Apt 3 bd Free Parking
3 bedrooms, 3 double beds, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 77 reviews
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds, 2 bathrooms
2–7 Nov
4.95 out of 5 average rating, 165 reviews
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Nov
4.96 out of 5 average rating, 305 reviews
Superhost
Flat in Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds, 3 bathrooms
1–6 Nov
4.9 out of 5 average rating, 122 reviews
Flat in Chicago
Stylish Flat near Downtown,Obama Library, UChicago
2 bedrooms, 2 queen beds, 1 bathroom
10–15 Sept
New place to stay
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 70 reviews
Top guest favourite
Flat in Chicago
Sun drenched 2 bedroom 1 bath with Kitchen & W/D
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.95 out of 5 average rating, 268 reviews
Top guest favourite
Flat in Forest Park
Like a Treehouse!
1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 383 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 27 reviews
Flat in Chicago
Art & Soul in Logan Square|4BR Walk to Blue Line
4 bedrooms, 4 beds, 1.5 bathrooms
17–22 Aug
New place to stay
Flat in Chicago
Kasa Lake Shore Chicago | Studio Queen
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
New place to stay
Top guest favourite
Apartment in Chicago
Wrigleyville Inn. Historic Greystone. Parking pass
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 174 reviews
Place to stay in Chicago
Charming Room in Historic Ukrainian Village!
1 bedroom, 1 queen bed, 1 bathroom
6–11 Sept
New place to stay
Top guest favourite
Flat in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms, 3 beds, 1 bathroom
30 Oct – 4 Nov
4.99 out of 5 average rating, 356 reviews